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GLUTINOSTERONE

Year of first isolation: 2015
Formula:C28H44O8
Molecular weight:508
Occurence in plants:
Sida glutinosa [Malvaceae] » Images of Sida glutinosa Wikipedia: Sida glutinosa [Malvaceae]
Occurence in animals:
 
GLUTINOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[C@@H]1([C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(=C)C(C)(C)O)O)O)O)C)C)O » JSMol: View in 3D
IUPAC Name(1S,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methyl-5-methyleneheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
XOXZUBARLRMAEA-ZCXRSSHBSA-N
InChIInChI=1S/C28H44O8/c1-14(24(2,3)34)11-21(31)27(6,35)20-8-10-28(36)16-12-18(29)17-13-19(30)22(32)23(33)26(17,5)15(16)7-9-25(20,28)4/h12,15,17,19-23,30-36H,1,7-11,13H2,2-6H3/t15-,17-,19+,20-,21+,22+,23+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

FAB-MS m/z (relative intensity %) 531 [M+Na]+ (4), 491 [MH - H2O]+ (33), 473 [MH - 2H2O]+ (38), 445 [MH - 3H2O]+ (67), 379 (21), 361 (21), 343 (25), 301 (25), 173 (29), 165 (29), 147 (21), 75 (100)
HR-FAB-MS m/s 531.2922 [M+Na]+, calculated for C28H44O8Na 531.1933; 509.2852 [M+H]+, calculated for C28H44O8 509.2862

CARBON NMR

PROTON NMR

CD3OD
0176.7 (d)
0268.7 (d)
0371.0 (d)
0432.9 (t)
0546.8 (d)
06206.0 (s)
07122.2 (d)
08167.5 (d)
0935.5 (d)
1043.6 (s)
1121.5 (t)
1232.9 (t)
1348.7 (s)
1485.1 (s)
1531.8 (t)
1621.5 (t)
1750.5 (d)
1818.1 (q)
1920.1 (d)
2077.9 (s)
2121.0 (q)
2277.5 (d)
2334.5 (t)
24155.3 (s)
2573.6 (s)
2632.0 (q)
2729.2 (q)
28110.4 (t)
CD3OD
01-He3.82 (br, d, 10.2)
02-Ha3.87 (ddd, 11.5, 4.0, 3.0)
03-He3.97 (br, q, 2.5)
04-Ha1.78 (dd, 15.6, 12.9)*
04-He1.64 (dd, 11.1, 7.5)*
05-H2.60 (br, d, 13.5)
07-H5.83 (br, s)
09-H3.17 (dd)
11-Ha1.64 (dd, 11.1, 7.5)
11-He 
12-Ha2.10 (dd, 11.4, 11.4)
12-He 
15-Ha1.80 (m)
15-Hb 
16-Ha2.02 (m)
16-Hb 
17-H2.40 (dd, 9.5, 8.5)
18-Me0.91 (s)
19-Me0.98 (s)
21-Me1.25 (s)
22-H3.61 (br, d, 10.5)
23-Ha2.39 (br, d, 13.5)
23-Hb2.14 (dd, 13.5, 8.5)
26-Me1.39 (s)
27-Me1.34 (s)
28-CH2=5.15 (a) (br, s), 4.97 (b) (br, s)

PHYSICAL PROPERTIES

M.P.230 °C (decomp.);
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)3389 (OH), 1658, 1642, 1464, 1445, 1381, 1150, 1059, 874
UV (EtOH) λ max (log ε)248 (3.61) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDAS, N. et al. (2015) J. Pharm. and Phytochem. 3, 73-78 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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